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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-23 01:33:43 UTC |
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Update Date | 2022-03-07 02:49:31 UTC |
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HMDB ID | HMDB0006351 |
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Secondary Accession Numbers | - HMDB0006207
- HMDB06207
- HMDB06351
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Metabolite Identification |
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Common Name | Vaccenyl carnitine |
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Description | Vaccenyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations. (PMID: 11999976 , 10682306 , 15025677 , 16168195 ). |
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Structure | CCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h10-11,23H,5-9,12-22H2,1-4H3/b11-10+/t23-/m0/s1 |
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Synonyms | Value | Source |
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O-(trans-Vaccenoyl)-D-carnitine | ChEBI | O-[(e)-Vaccenoyl]-D-carnitine | ChEBI | Acylcarnitine C18:1 | HMDB | R-(11E Octadecenoyl) carnitine | HMDB |
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Chemical Formula | C25H47NO4 |
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Average Molecular Weight | 425.654 |
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Monoisotopic Molecular Weight | 425.350508997 |
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IUPAC Name | (3S)-3-[(11E)-octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoate |
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Traditional Name | (3S)-3-[(11E)-octadec-11-enoyloxy]-4-(trimethylammonio)butanoate |
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CAS Registry Number | Not Available |
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SMILES | CCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C |
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InChI Identifier | InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h10-11,23H,5-9,12-22H2,1-4H3/b11-10+/t23-/m0/s1 |
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InChI Key | HOAMADDCQBUDDY-YSESTWPTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acid esters |
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Direct Parent | Acyl carnitines |
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Alternative Parents | |
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Substituents | - Acyl-carnitine
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid salt
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 220.676 | 30932474 | DeepCCS | [M-H]- | 217.416 | 30932474 | DeepCCS | [M-2H]- | 251.666 | 30932474 | DeepCCS | [M+Na]+ | 228.173 | 30932474 |
Predicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Vaccenyl carnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Vaccenyl carnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Positive-QTOF | splash10-05r3-0953800000-10c117f27cdeca6b78e8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Positive-QTOF | splash10-0006-1920000000-454f3fd140a9f3a75952 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Positive-QTOF | splash10-006x-4940000000-cf06ad95e45d27992e00 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Negative-QTOF | splash10-00di-1031900000-560a56638a8a770c6886 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Negative-QTOF | splash10-00yi-1179400000-ed01fc9b8478ba25da72 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Negative-QTOF | splash10-06s6-5090000000-92221a20e063037e4db4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Positive-QTOF | splash10-004i-0000900000-c76c8c1a67e6b24de5c1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Positive-QTOF | splash10-002r-9000500000-4902a8769b2895518a15 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Positive-QTOF | splash10-000i-9000000000-e9262cbaff8cb4ad0ba6 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Mitochondria
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023900 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 64808356 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | 2614385 |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53477830 |
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PDB ID | Not Available |
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ChEBI ID | 136372 |
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Food Biomarker Ontology | Not Available |
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VMH ID | OCDECECRN |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Reuter SE, Evans AM, Faull RJ, Chace DH, Fornasini G: Impact of haemodialysis on individual endogenous plasma acylcarnitine concentrations in end-stage renal disease. Ann Clin Biochem. 2005 Sep;42(Pt 5):387-93. [PubMed:16168195 ]
- Gempel K, Kiechl S, Hofmann S, Lochmuller H, Kiechl-Kohlendorfer U, Willeit J, Sperl W, Rettinger A, Bieger I, Pongratz D, Gerbitz KD, Bauer MF: Screening for carnitine palmitoyltransferase II deficiency by tandem mass spectrometry. J Inherit Metab Dis. 2002 Feb;25(1):17-27. [PubMed:11999976 ]
- Shen JJ, Matern D, Millington DS, Hillman S, Feezor MD, Bennett MJ, Qumsiyeh M, Kahler SG, Chen YT, Van Hove JL: Acylcarnitines in fibroblasts of patients with long-chain 3-hydroxyacyl-CoA dehydrogenase deficiency and other fatty acid oxidation disorders. J Inherit Metab Dis. 2000 Feb;23(1):27-44. [PubMed:10682306 ]
- Spiekerkoetter U, Tokunaga C, Wendel U, Mayatepek E, Exil V, Duran M, Wijburg FA, Wanders RJ, Strauss AW: Changes in blood carnitine and acylcarnitine profiles of very long-chain acyl-CoA dehydrogenase-deficient mice subjected to stress. Eur J Clin Invest. 2004 Mar;34(3):191-6. [PubMed:15025677 ]
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